Every Bridge Burned
by Soulhates
Summary: At his sensei's dying request, Naruto sets off from home on a mission to deliver two letters, both addressed to individuals he has never heard of before – a Tsunade and an Orochimaru. Along the way, he gains several strange companions, like an ambitious thief named Sakura and a left-handed swordsman named Sasuke. AU, pairings undecided.


**A/N: This is somewhat inspired by the anime Samurai Champloo, so the time period is similar – a sort of feudal/Edo period Japan that probably has some historical inaccuracies to fit the plot.**

Chp 1: Decisions Made

Even at his deathbed, Jiraiya still retained a great deal of his old jovial self. It was far from his right time to go, though one could argue there never will be a right time for him, but a malignant growth in his vitals region waited for no man.

For the past week or so, Naruto Uzumaki has seen his beloved sensei and old family friend eat barely a thing and sleep for a large majority of the days. Due to the man's decreased ability to take care of himself, Naruto's parents, Minato and Kushina, have insisted that he come and live in their guest room (though Jiraiya's own house was not situated too far away).

There, it proved much easier to keep an eye on his condition, though the idea of too much dependency didn't sit very well with the sick man. Nonetheless, he complied.

The living situation did have some of its own merits, though, as Naruto did find it more convenient to seek out Jiraiya whenever he needed some guidance on any subject.

As to what those subjects were, well, it varied quite dramatically. One second Jiraiya would be telling the boy about the best pickup lines sure to impress girls, and the next, he would be giving him some pointers on his sword fighting technique. Jiraiya didn't actively participate in those lessons, of course, as picking up and swinging a sword around wouldn't prove too helpful for the pain in his stomach, but he observed his student from the sidelines and liberally handed out critiques.

When Minato and Kushina first discovered, seven years back, that their old acquaintance Jiraiya has moved in nearby, they immediately paid him a visit. Turns out, the man decided to permanently retire from his adult novel writing career and was hoping to live the rest of his life in peace and semi-isolation.

Unexpected as their visit was, he soon opened up to the Uzumakis and found out they were stuck in a serious dilemma.

Their child, a very hyperactive, loud-mouthed ten-year-old, proved too much to handle for all the conventional schools and teachers in the village and therefore was left instructor-less. Part of the problem was also due to the boy's left handedness, as no amount of proper correction from anyone could seem to make him use his right one.

Everyone knew that in order to be well-rounded and respected back then, a person must be fluent in literature and poetry, arithmetic, and the ways of the sword. The Uzumakis had wanted that for their child, for him to have success later on in life, no matter how impeded he was in that pursuit.

But with no suitable instructors who even wanted to teach the boy... well, they were in a bit of a pickle.

Then came their savior in the form of Jiraiya, oh the esteemed Jiraiya who fit all the qualifications of a jack-of-all-trades. He was a published author (though they have never read any of his novels), not bad with numbers, and especially skilled in martial arts.

The man had taken on good look at the rambunctious Naruto and deemed him a challenge worthy enough of his instruction.

Part of him accepting the position was because of his past friendly affiliations with Minato, but he also wasn't the type to back down from a difficult case, retirement be damned. If Naruto was such a hard egg to crack for everyone else, then he'd have to be the first one to crack it.

There were moments when the boy's parents questioned the orthodoxy of the man's methods – like stealth training in a _bath house_? What had that been all about? – but ultimately, the results were there.

Naruto was far from a scholar, having limited interest in the more academic subjects, but his swordsmanship soared as he showed a natural aptitude for more impressive was how he managed, through it all, to stick with his left hand using special moves designed by Jiraiya himself.

In all the dojos that the boy has visited before, they taught the standard moves and stances fit for the right side. Anyone unfortunate enough to be stricken with the opposite handedness was forced to adjust, as they are seen to be deviating from the correct method of doing things. Obvious, that was a system which proved utterly ineffective on Naruto, as he was a complete klutz with his non-dominant hand, so he has never gone back to any of the dojos since.

Now, before everyone knew it, the blond was able to hold his own against any dojo-bred, correct-handed swordsman without too much trouble. What's more, as most opponents have never fought someone with the same habits as him before, there was a clear advantage before the matches even began.

But alas, skilled and well endowed in some aspects Jiraiya might be, but his health was lacking. It took months for the symptoms to first visibly manifest in the form of stomachaches, but when it did hit, the sickness advanced swiftly. With some consternation, he informed his caretakers that his mother had been inflicted with the same thing as he had.

Locals doctors have been called, but no luck. Desperate, Minato has even invited over faith healers, but that was useless as well.

Jiraiya seemed to be pretty aware of his own morality and knew he was going to be finished soon, so on one of his better days, he called his pupil over for a bit of a heart-to-heart, as was customary.

He tried to start the conversation off on the lighter side of the spectrum, while leaning back from his sitting position on the bed: "You know what's the worst part about dying right now, Naruto?"

Naruto fidgeted at the question and scratched the back of his head, unsure whether it was meant as a joke or not. Deciding to hell with it, he replied with his usual perk, "Um, you won't be able to spy on all the shirtless women in the bath houses anymore?"

A guffaw erupted from his mouth, "Oh yes, I had completely forgotten about that. But my, eh, research aside, I'd say it has to be never getting enough time to write another novel again." He paused. "And just when I've gotten a sudden burst of inspiration for a new novel, the first since my permanent hiatus from the _Icha Icha_ series. I was planning it to be one of my best stories, too."

Though Naruto has requested on multiple occasions to read his past works, Jiraiya has always denied the request and said it wasn't the best idea. He never gave a reason why.

Continuing on, the older man said, "My new book was going to start off with a young boy who is, to put it kindly, a loser. His whole village shuns him because sealed inside his body is a demon spirit that ravaged the people's land years before, when he was still a baby. To transcend above his years of loser-dom, the boy wants to be the greatest ninja in his village, a title called the Hokage. Along the way, he gets help from a few friends. It's going to be called _Tales of a Gutsy Ninja_, and that's how far I've got planned."

"Sounds good. But you shouldn't be so down about it all. If you start writing it now, who knows, maybe you could have it done before –" Okay, that sounded ridiculous, even to Naruto himself. Going down a different path, he snapped his fingers like a great idea just struck him. "I could write the book for you, if you want."

A wide smile began to spread across Jiraiya's face. "Yes, of course! How did I not think of that?"

"Just tell me a bit more about the set-up," he looked excitedly around the room for some paper, "and I'll be sure to have it become the next bestseller. So, what's the boy's name gonna be?"

"Naruto."

"Yeah?"

"No, I meant that's the name of the boy."

"Oh." The blond fell silent, and his expression lost some of its usual cheer. Giving up on his mission to look for some scratch paper, he said more somberly, "You don't seem to be very upset at all. How are you still so, I don't know, casual about... about..."

"About dying? I'll let you in on a secret, Naruto," he gestured for his student to come closer, and the boy complied. "The trick is to live a satisfied life, and the trick to a satisfied life is not having any regrets. That's also part of the reason why I wanted to talk to you in private today. It's rather important."

Seeing his sensei suddenly turn so serious about this new matter, Naruto changed his demeanor to match. "What is it?"

"You see, I did my best to live my life and not have any regrets about anything, but there are just two things that ruined my pristine record. Two people, actually. And since I'm in no position to leave this house anytime soon, I won't be able to clear that record, and it's going to bug me senselessly. Which is why I need your help in clearing it."

A bit puzzled, "Me?"

Jiraiya reached for two sealed envelopes, which rested on a small table beside the bed that Naruto only noticed now. He handed them to his protegée.

There was a name on each – "Tsunade" and "Orochimaru." Curiosity piqued, Naruto looked up and eagerly waited for an explanation.

"They used to be friends of mine, but I haven't seen them in decades. All I want you to do is deliver these letters to them, and that'll wipe everything that's still sticking to the back of my conscience."

Naruto weighed the papers in his hand. Light as the pages might be, the significance was not lost on him. Jiraiya was basically asking to be brought peace in death, and that was as heavy a responsibility as anyone can have over someone else. "Where are they now?"

The man frowned. "The problem is, I'm not sure. We haven't kept in touch, so who knows where they've moved. As for Tsunade, the last I've heard is that she was in the northern city of Konoha. Orochimaru is a bit of a migrant, so he's more elusive. But I'm sure Tsunade would know. And if not, well, I'd just be grateful knowing my slate has one less stain on it."

Pocketing the letters, Naruto gave his most reassuring grin, slipping away from his serious persona. "Don't worry, I'll find them, and they'll read the letter even if I have to threaten them."

"Thank you." Had there been a competition for genuine gratitude, Jiraiya would've won by a landslide at that moment. He closed his eyes in satisfied relaxation. "You didn't turn out half bad, you know that? From that way too jumpy ten-year-old kid to what you are now."

"I'll take that as a compliment."

"It was."

* * *

Some intuition the old man must've had, picking that specific day to speak with Naruto, because his death came barely 48 hours after.

At the funeral, which was a small event, no tears had come out of the now sensei-less boy's eyes. Maybe it was the surrealistic feel of the whole event, but he simply stood by the sidelines and watched, stony eyed. The finality of it couldn't seem to reach him yet.

It was only a day after that the waterworks proved functional.

Following the funeral, he retired to the privacy of his room and spent hours upon hours trying to start the first chapter of _The Tales of a Gutsy Ninja_. He had managed to get more about the story out of Jiraiya during the span of their conversation and his death – like how the demon sealed inside the boy was a nine-tailed fox spirit – but still, he couldn't write past the first sentence.

He had rewritten it over a dozen times.

_The nine-tailed fox, a formidable creature which _– scratched out.

_An isolated child by the name of Naruto _– crumbled up and tossed away.

_How fragile and delicate peace must be, because it was completely shattered when _– ripped into shreds.

"Aaah!" He had bursted out in frustration. One can only tolerate so many consecutive failures. It also took a minute for him to notice the wetness on his cheeks. Hm, salty.

Shoving all the papers and discarded drafts to the corner of his desk, Naruto crawled into the comfort of his bed. Bringing his knees up to his chest into a fetal position, he stayed like that for many crawling hours.

Not even Minato and Kushina's soft voices could seem to penetrate the fortress of blankets and grief.

* * *

It took three whole days before Naruto was able to compose himself, change into fresh clothes, and have a meal at all in a location outside his own room. But when the change did come, it was sudden and spectacular.

He must've gone through a mental metamorphosis overnight, because even his parents looked surprised at his sudden appearance at breakfast when as recent as last night, he was holed up in his room and didn't wish to speak to them. Now, there was a fresh determination in those blue eyes, which replaced the downtrodden look that had been there not so long ago.

"Are you... feeling better?" Minato ventured.

His son nodded and began to inhale mouthfuls of food, hunger intensified by the lack of it over the span of these past few days.

"Be careful that you don't choke," Kushina warned, but nonetheless shoving two more bowls that are filled to the brim towards him.

When he was finished with all _that_, he finally spoke between gasps for air. "I'm leaving today."

"What? No you're not." There was a frown on Kushina's face.

Naruto could usually tell what his mother's emotional state was by the way she handles her hair, and seeing how she began to aggressively finger-comb it, he quickly jumped in to give an explanation, "N-not permanently, don't worry. I'm just taking a temporary... trip, I guess. Before he died, Jiraiya asked me to do a favor for him. And I need to keep my promises."

Minato was listening with quiet intrigue while Kushina seemed to be mentally formulating arguments against her son.

"Besides, I thought it all over last night and decided this could be my chance to get out of this bubble, you know? I'm already seventeen and haven't stepped foot outside this village yet!" He wasn't the best at articulating his feelings eloquently, but this was a speech he'd already practice many times. The part about the bubble added in as more incentive for his parents letting him go.

"First off –" Kushina began, only to be interrupted by Minato, who said, "I think that's a great idea, actually."

"What?" The red-haired woman turned towards her husband and protested, "But there are murderers out there! Also thieves, cannibals, and those damn, pesky pirates I've been hearing stories about recently."

"Well, Naruto didn't learn to use a sword for nothing," Minato countered easily.

Now that he had his father on his side, Naruto knew they held the advantage with their two-on-one majority. Kushina must've realized she was outnumbered and outmatched, because she backed off from actively opposing the trip. In a more concerned tone, she asked, "What's this favor he asked you to do?"

"To deliver two letters –"

She relaxed; that seemed innocuous enough.

" – to a city called Konoha."

The frown returned. "But isn't that all the way up in the north, if I remember my geography correctly? It'd take weeks, maybe even months, to travel up there!"

"I'll take enough supplies."

Minato laid a hand on his anxious wife's shoulder, "Don't worry, it'll be like a sightseeing trip. He'll be able to see so much of the country with one go, and the experiences are invaluable. Besides, we have an obligation to honor Jiraiya's last wishes, seeing how he was so courteous to train and teach Naruto all these years."

A prolonged moment of contemplation later, Kushina inquired, "And when do you intend to leave?"

"I was thinking maybe now."

"Now?!"

"I've already got everything packed, so there's no reason to delay. Wait, I'll show you." The boy jumped to his feet and scampered off towards his room. A little while later, he returned in his signature outfit of dulled orange and black, a sword strapped to his right side, and a cloth bundle slung across his back. He gave a slow, 360 pivot in front of his parents.

Kushina was on him in a second while Minato watched the spectacle unfold with an amused chuckle. "You can't go off with your hair looking like that – you're representing the Uzumaki family here! And what'd you bring in your bag? That's it? I'm gonna give you some of the pastries I made this morning to put in there. How much money are you bringing? You really shouldn't keep it tucked so loosely behind your shirt like that! Do you know how easily it could fall out?"

"Mom, mom," He squirmed and managed to slip out of the range of her poking and prodding. "I'll be fine. I know what I'm doing."

She finally paused and gave her son a careful once-over. Satisfied, she pulled him into a bear hug and whispered into his ear, "Come back in one piece, you hear? And stay clear of those pirates."

"Yes, mom," he managed to choke out. "I – can't breathe."

Freed from the woman's death grip, he gave her a sheepish smile and turned to his father. Minato wore a smile as well, but instead of Kushina's intense embrace, he gave a brief but firm one-armed hug, whispering some travel tips to him as well.

Naruto didn't hang around for too long after that. A double-check of all his supplies and more fussing from his mother later, he took that fresh step full of promises out the threshold of the house.

It was looking up to be a beautiful day indeed.

_Next Chapter: A pink-haired girl... some law enforcement officers on the chase... a sudden burst of inspiration._

**A/N: I know Naruto's right-handed in canon, but changing it will be significant to the story later on. He was also a bit down this chapter, and that might make his a bit OOC, but I promise the mood will pick up.**

**I'd love a review, and thanks for reading! :]**


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